The goal of this study is to establish a general protocol whereby N-substituted or (ultimately) N-unsubstituted amide functions may be directly emplaced at molecular carbonyl sites (to form alpha-hydroxyamides) or at imino sites (to form alpha-aminoamides). Amide-containing compounds (or the corresponding amines obtainable by amide reduction) are widely distributed amongst valuable therapeutic agents. The application of carbamoylsilanes to this end will be explored by extending successful preliminary results to a wide spectrum of candidate co-reactants under catalytic or noncatalytic conditions with a view towards maximizing output yields under the mildest possible conditions. Exploratory experiments directed towards inducing chiral stereoselectivity within these transformations will also be carried out.